Atorvastatin lactone

Base Information

• Chemical Name: Atorvastatin lactone
• CAS No.: 125995-03-1
• Molecular Formula: C33H33FN2O4
• Molecular Weight: 540.634
• Hs Code.: 2934999090
• European Community (EC) Number: 418-950-3,642-043-3
• UNII: 7876IL7J2N
• DSSTox Substance ID: DTXSID90155033
• Nikkaji Number: J360.189G
• Wikidata: Q27074604
• Pharos Ligand ID: VA22T5QH2AFL
• ChEMBL ID: CHEMBL333687
• Mol file: 125995-03-1.mol

Synonyms:Atorvastatin lactone;125995-03-1;UNII-7876IL7J2N;5-(4-fluorophenyl)-1-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-N,4-diphenyl-2-propan-2-ylpyrrole-3-carboxamide;7876IL7J2N;Atorvastatin delta-Lactone;CHEMBL333687;(+)-ATORVASTATIN LACTONE;DTXSID90155033;5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide;1H-Pyrrole-3-carboxamide, 5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-;5-(4-Fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1H-pyrrole-3-carboxamide;(4R,6R)-6-[2-[2-(4-Fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl]ethyl]-4-hydroxytetrahydro-2H-pyran-2-one (Atorvastatin Lactone);1H-PYRROLE-3-CARBOXAMIDE, 5-(4-FLUOROPHENYL)-2-(1-METHYLETHYL)-N,4-DIPHENYL-1-(2-(TETRAHYDRO-4-HYDROXY-6-OXO-2H-PYRAN-2-YL)ETHYL)-, (2R-TRANS)-;1H-Pyrrole-3-carboxamide, 5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-;5-(4-FLUOROPHENYL)-1-(2-((2R,4R)-4-HYDROXY-6-OXOTETRAHYDROPYRAN-2-YL)ETHYL)-2-ISOPROPYL-4-PHENYL-1H-PYRROLE-3-CARBOXYLIC ACID PHENYLAMIDE;5-(4-Fluorophenyl)-1-{2-[(2R, 4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide;Atorvastatin IMpurity H;Impurity H;Ethylmorphine-d5;5-(4-Fluorophenyl)-1-[2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl]-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide;Atorvastatin EP Impurity H;MLS006010799;GTPL2957;SCHEMBL1258955;DTXCID4077524;SCHEMBL13900415;ATORVASTATIN LACTONE [MI];OUCSEDFVYPBLLF-KAYWLYCHSA-N;5-(4-fluorophenyl)-1-[2-[(2S,4R)-4-hydroxy-6-oxo-2-oxanyl]ethyl]-N,4-diphenyl-2-propan-2-yl-3-pyrrolecarboxamide;ATORVASTATIN .DELTA.-LACTONE;BDBM50011032;MFCD00899262;AKOS015896169;CS-O-07292;DS-4553;5-(4-fluorophenyl)-1-[2-[(2R,4R)-4-hydroxy-6-oxo-tetrahydropyran-2-yl]ethyl]-2-isopropyl-N,4-diphenyl-pyrrole-3-carboxamide;SMR002529529;HY-101873;CS-0022115;F52842;J-005315;ATORVASTATIN CALCIUM IMPURITY H [EP IMPURITY];Q27074604;(2R trans)-5 (4-fluorophenyl)-2 (1-methylethyl) -N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide;(2R-trans)-5-(4-fluorophenyl)-2(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4hydroxy-6-oxo-2H-pyran-2-yl)-ethyl]-1H-pyrrole-3carboxamide;(2R-Trans)-5-(4-fluorophenyl)-2-(1-methyl -ethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo -2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide;(2R-trans)-5-(4-fluorophenyl)-2-(1-methyl-ethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide;(2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro -4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide;(2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)-ethyl]-1H-pyrrole-3-carboxamide;(2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)-ethyl]-1H-pyrrole-3carboxamide;(2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)-ethyl]1H-pyrrole-3-carboxamide;(2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide;(2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide;5-(4-Fluoro-phenyl)-1-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide;5-(4-fluorophenyl)-1-[2-((2R,4R)-4-hydroxy -6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide;5-(4-fluorophenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran -2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide;5-(4-fluorophenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide;5-(4-fluorophenyl)-1-[2-((2R,4R)4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide;5-(4-fluorophenyl)-1-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-N,4-diphenyl-2-(propan-2-yl)-1H-pyrrole-3-carboxamide

Chemical Property of Atorvastatin lactone

Chemical Property:

• Appearance/Colour: slightly yellow solid
• Vapor Pressure: 3.92E-19mmHg at 25°C
• Melting Point: 103-106 °C
• Refractive Index: 1.616
• Boiling Point: 674.8 °C at 760 mmHg
• PKA: 13.39±0.40(Predicted)
• Flash Point: 361.9 °C
• PSA: 80.56000
• Density: 1.24 g/cm³
• LogP: 6.86650
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 540.24243570
• Heavy Atom Count: 40
• Complexity: 834

Purity/Quality:

99% ^*data from raw suppliers

Atorvastatin Lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C(=C(N1CCC2CC(CC(=O)O2)O)C3=CC=C(C=C3)F)C4=CC=CC=C4)C(=O)NC5=CC=CC=C5
• Isomeric SMILES: CC(C)C1=C(C(=C(N1CC[C@@H]2C[C@H](CC(=O)O2)O)C3=CC=C(C=C3)F)C4=CC=CC=C4)C(=O)NC5=CC=CC=C5
• Uses: Atorvastatin intermediate as inhibitor of MAP kinase and/or HMG-CoA reductase for the treatment of inflammation Atorvastatin Lactone (Atorvastatin EP Impurity H) is an intermediate of Atorvastatin, a inhibitor of MAP kinase and/or HMG-CoA reductase for the treatment of inflammation.

Technology Process of Atorvastatin lactone

There total 60 articles about Atorvastatin lactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

pentan-1-ol (71-41-0) + lipitor (134523-03-8) → pentyl (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate + atorvastatin lactone (125995-03-1)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃; for 2.58333h;

DOI:10.1080/00498254.2019.1625083

Reference yield: 95.0%

1-[2-((2R,4R)-4,6-dihydroxytetrahydro-2H-pyran-2-yl)ethyl]-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide (842163-03-5) → atorvastatin lactone (125995-03-1)

Guidance literature:

With manganese(IV) oxide; In acetone; at 25 ℃; for 24h;

DOI:10.1039/c5ob02546j

Reference yield: 90.0%

2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid (581772-29-4) → atorvastatin lactone (125995-03-1)

Guidance literature:

With camphor-10-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2010.10.028

upstream raw materials:

(R^*,R^*)-3,5-dihydroxy-7-<(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-<(phenylamino)carbonyl>-1H-pyrrol-1-yl>-1-heptanoic acid

α-<<2-(1,3-dioxolan-2-yl)ethyl>(2-methyl-1-oxopropyl)amino>-4-fluorobenzeneacetic acid

α-<<2-(1,3-dioxolan-2-yl)ethyl>(2-methyl-1-oxopropyl)amino>-4-fluorobenzeneacetic acid, ethyl ester

5-(4-fluorophenyl)-2-(1-methylethyl)-1-(3-oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide

Downstream raw materials:

(-)-(4S)-trans-2-(4-fluorophenyl)-5-(1-methylethyl)-N,3-diphenyl-1-<(tetrahydro-4-hydroxy-2-oxo-2H-pyran-6-yl)ethyl>-1H-pyrrole-4-carboxamide

atorvastatin potassium

atorvastatin sodium

tetraethyl [(3R,5R)-(7-(3-(phenylcarbamoyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoyl)aminomethylene]bisphosphonate

Refernces

• 1、 Bogman, Katrijn,Peyer, Anne-Kathrin,Toeroek, Michael,Kuesters, Ernst,Drewe, Juergen. "HMG-CoA reductase inhibitors and P-glycoprotein modulation". . p. 1183 - 1192. Retrieved 2001.
• 2、 -. "NOVEL CLASS OF COMPOUNDS FOR THE TREATMENT OF CARDIOVASCULAR DISEASE". Page/Page column 62. . Retrieved 2017/09/05.